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693049

(R)-Tol-BINAP

Name: (<I>R</I>)-Tol-BINAP
Brand: ALDRICH

Synonym(s):

(R)-(+)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl

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About This Item

Empirical Formula (Hill Notation):

C₄₈H₄₀P₂

CAS Number:

99646-28-3

Molecular Weight:

678.78

MDL number:

MFCD01311709

UNSPSC Code:

12352005

PubChem Substance ID:

329761557

NACRES:

NA.22

form

solid

optical activity

[α]20/D +162°, c = 0.5 in benzene

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Cross Couplings

mp

254-258 °C

functional group

phosphine

SMILES string

Cc1ccc(cc1)P(c2ccc(C)cc2)c3ccc4ccccc4c3-c5c(ccc6ccccc56)P(c7ccc(C)cc7)c8ccc(C)cc8

InChI

1S/C48H40P2/c1-33-13-23-39(24-14-33)49(40-25-15-34(2)16-26-40)45-31-21-37-9-5-7-11-43(37)47(45)48-44-12-8-6-10-38(44)22-32-46(48)50(41-27-17-35(3)18-28-41)42-29-19-36(4)20-30-42/h5-32H,1-4H3

InChI key

IOPQYDKQISFMJI-UHFFFAOYSA-N

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General description

BINAP is based on a bis naphthalene backbone with different phosphine derivatives. 2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl (p-Tol-BINAP)·AgF complex catalyzed asymmetric Mukaiyama-type aldol reaction is reported.

Application

Takasago Ligands and Complexes for Asymmetric Reactions

(R)-T-BINAP complexes derived from rhodium precursors are used for the asymmetric hydroformylation of vinyl acetate. It may be employed as chiral catalyst for allylation of N-tosyl α-imino esters.

Catalyst involved in studies of the role of excess phosphine ligand in enantioselective conjugate addition of ethylmagnesium bromide and α,β-unsaturated ester

Reactant serving as a precursor for:

Catalysts used for reductive amination of ketones
Rh(I)-catalyst for hydrogenation of acetamidoacrylic acid derivatives
Chiral platinum catalysts for asymmetric Baeyer-Villiger oxidation of cyclic ketones
CuI-Tol-BINAP catalysts for enantioselective Michael reactions of Grignard reagents to unsaturated esters
BINAP Pt Dications for cation trapping

Legal Information

Sold in collaboration with Takasago for research purposes only.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Catalytic Approach for the Formation of Optically Active Allyl alpha-Amino Acids by Addition of Allylic Metal Compounds to alpha-Imino Esters.

Xiangming Fang et al.

The Journal of organic chemistry, 64(13), 4844-4849 (2001-10-25)

A new catalytic enantioselective approach for the formation of allyl alpha-amino acid derivatives by reaction of N-tosyl alpha-imino esters with allyl stannanes and silanes catalyzed by chiral copper(I) complexes has been developed. A series of different BINAP and phosphine-oxazoline (P,N)

Catalytic Asymmetric Aldol Reaction of Trimethoxysilyl Enol Ethers Using 2, 2'-Bis (di-p-tolylphosphino)-1, 1'-binaphthyl AgF Complex.

Yanagisawa A, et al.

Bulletin of the Chemical Society of Japan, 74(8), 1477-1484 (2001)

Asymmetric hydroformylation of vinyl acetate with BINAP-rhodium (I) complexes.

Hoegaerts D and Jacobs PA.

Tetrahedron Asymmetry, 10(15), 3039-3043 (1999)

Articles

Baeyer-Villiger Oxidation Reaction

The Baeyer-Villiger oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts the ketones to esters and the cyclic ketones to lactones.

BINAP/SEGPHOS® Ligands and Complexes

We present an article concerning BINAP/SEGPHOS® Ligands and Complexes.

Takasago Ligands

Hydrogenation, Asymmetric Catalysis, Binap, SEGPHOS®, Aldol reaction, Alkenylation, Arylation, Mannich reaction, Fluorination, Michael addition, Hydrosilylation, Cycloaddition, Takasago

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